N±-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine, CAS No. 90013-45-9

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90013-45-9

Catalog No. EBD681792

CAS 90013-45-9

Name N±-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine

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Basic Information

Synonyms: L-serine,O-[bis(phenylmethoxy)phosphinyl]-N-[(1,1-dimethylethoxy)carbonyl]- O-[Bis(benzyloxy)phosphoryl]-N-(tert-butoxycarbonyl)-L-serine (2S)-2-(tert-butoxycarbonylamino)-3-dibenzyloxyphosphoryloxy-propanoicacid Boc-O-Dibenzylphospho-L-Serine N±-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine N±-t-butoxycarbonyl-O-(dibenzylphosphono)-L-serine N±-(t-butyloxycarbonyl)-O-(dibenzylphosphoro)-L-serine Boc-Ser(PO3Bzl2)-OH n-alpha-boc-o-(dibenzylphospho)-l-serine nα-boc-o-(dibenzylphospho)-l-serine 11-mercaptoundecanoicacid,mua,muda n^a-boc-o-(dibenzylphospho)-l-serine,96% (s)-3-((bis(benzyloxy)phosphoryl)oxy)-2-((tert-butoxycarbonyl)amino)propanoicacid

Molecular Formula: C22H28NO8P

Molecular Weight: 465.43

MDL Number: MFCD00080284

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds

Product Description:

N-Boc-O-(dibenzylphosphono)-L-serine is a protected serine derivative featuring both a tert-butoxycarbonyl (Boc) group on the amine and a dibenzylphosphono group on the hydroxyl side chain. This specific protection pattern makes it a valuable chiral building block in peptide and peptidomimetic chemistry. Its primary application is in the synthesis of phosphonopeptides, which are analogs of natural peptides where the hydrolytically labile phosphate ester bond is replaced by a more stable phosphonate group. These compounds are of significant interest in medicinal chemistry as potential enzyme inhibitors, particularly targeting proteases and kinases. The Boc-protected amine allows for selective deprotection under mild acidic conditions, facilitating further chain elongation in solid-phase or solution-phase peptide synthesis. The dibenzylphosphono moiety serves as a precursor to the phosphonic acid or phosphonate ester functionality in the final target molecule. After incorporation into the peptide sequence, the benzyl groups can be removed via hydrogenolysis to reveal the free phosphonic acid. This compound is therefore a specialized, application-oriented synthon rather than a general-purpose reagent.

Physical Properties

Boiling Point: 626.9°C at 760 mmHg

Flash Point: 333°C

Density: 1.273g/cm3

Storage: 2-8°C